WO2018056546A1 - 신규한 화합물, 코어-쉘 염료, 이를 포함하는 감광성 수지 조성물 및 컬러필터 - Google Patents

신규한 화합물, 코어-쉘 염료, 이를 포함하는 감광성 수지 조성물 및 컬러필터 Download PDF

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WO2018056546A1
WO2018056546A1 PCT/KR2017/004956 KR2017004956W WO2018056546A1 WO 2018056546 A1 WO2018056546 A1 WO 2018056546A1 KR 2017004956 W KR2017004956 W KR 2017004956W WO 2018056546 A1 WO2018056546 A1 WO 2018056546A1
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Prior art keywords
core
formula
compound
shell
resin composition
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PCT/KR2017/004956
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English (en)
French (fr)
Korean (ko)
Inventor
정의수
박채원
서혜원
신명엽
신선웅
최규범
한규석
Original Assignee
삼성에스디아이 주식회사
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Application filed by 삼성에스디아이 주식회사 filed Critical 삼성에스디아이 주식회사
Priority to JP2019514764A priority Critical patent/JP6761118B2/ja
Priority to CN201780056576.1A priority patent/CN109715600B/zh
Priority to US16/308,853 priority patent/US11041073B2/en
Publication of WO2018056546A1 publication Critical patent/WO2018056546A1/ko

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/007—Squaraine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B55/00—Azomethine dyes
    • C09B55/002—Monoazomethine dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/64—Quaternary ammonium compounds having quaternised nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/10—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

Definitions

  • Novel compounds, core-shell dyes, photosensitive resin compositions and color filters comprising the same
  • the present disclosure relates to a novel compound, a core-shell dye, a photosensitive resin composition comprising the same, and a color filter manufactured using the same.
  • the liquid crystal display device which is one of the display devices, has advantages such as light weight, thinness, low cost, low power consumption, and excellent bonding with an integrated circuit, and its use range is expanding for notebook computers, monitors, and TV images.
  • the liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and a ⁇ pixel electrode are formed, an active circuit unit consisting of a liquid crystal layer, a thin film transistor, and a capacitor capacitor layer, and an upper substrate on which an IT0 pixel electrode is formed.
  • the color filter includes a black matrix layer formed in a predetermined pattern on a transparent substrate to shield the boundary between pixels, and a plurality of colors, typically red (R), green (G), blue (B), to form each pixel. ) Has a structure in which the pixel portions arranged in the predetermined order in the three primary colors are stacked one by one.
  • the pigment dispersion method which is a method of implementing a color filter, coats a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix, exposes a pattern of a shape to be formed, and then removes non-exposed areas with a solvent. It is a method in which a colored thin film is formed by repeating a series of processes of thermal curing.
  • the colored photosensitive resin composition used for manufacturing the color filter by the pigment dispersion method generally consists of alkali-soluble resin, a photopolymerizable monomer, a photoinitiator, an epoxy resin, a solvent, other additives, etc.
  • the pigment dispersion method is actively used for manufacturing LCDs of mobile phones, notebook computers, monitors, TVs, and the like.
  • the excellent pattern characteristics in the photosensitive resin composition for color filters using a pigment dispersion method having various advantages but also Better performance is required.
  • high brightness and high contrast ratio characteristics are urgently required.
  • the image sensor refers to an image pickup device component that generates an image from a mobile phone camera or a digital camera (DSC), and is a solid-state image pickup device (charg6 coupled devi ce, CCD) according to its manufacturing process and application method. It can be classified into an image sensor and a complementary metal oxide semiconductor CMOS image sensor.
  • Color image pickup devices used in solid-state image pickup devices or complementary metal oxide semiconductors have a color filter including a red, green, and blue addition and mixing filter segments of red, green, and blue on the light receiving device. It is common to install (color filters) separately and color-decompose them.
  • the size of the color filter mounted on such a color image pickup device is 2 or less, which is 1/100 to 1/200 times the size of the conventional color filter pattern for LCD. Accordingly, the increase in resolution and the reduction of residues are important factors that determine the performance of the device.
  • One embodiment is to provide a novel compound excellent in brightness and contrast ratio.
  • Another embodiment is to provide a core-shell dye comprising the novel compound.
  • Another embodiment comprises the novel compound or core-shell dye It is for providing the photosensitive resin composition.
  • Another embodiment is to provide a color filter using the photosensitive resin composition.
  • One embodiment provides a compound represented by Formula 1 below.
  • R 1 is a substituted or unsubstituted C3 to C20 cycloalkyl group or represented by the following formula (2),
  • R 2 is a substituted C6 to C20 aryl group
  • R 3 and R 4 are each independently a substituted or unsubstituted C 1 to C 10 alkyl group.
  • R 2 may be a C 6 to C 20 aryl group substituted with a C 1 to C 10 alkyl group.
  • R 2 may be represented by the following Chemical Formula 3.
  • R 5 and R 6 are each independently a C1 to C7 alkyl group.
  • the compound represented by Chemical Formula 1 may be represented by any one selected from the group consisting of compounds represented by Chemical Formulas 1-1 to 1-7.
  • Another embodiment includes a core comprising a compound represented by Formula 1; And it provides a core-shell dye comprising a shell surrounding the core.
  • the sal may be represented by the following formula (4) or (5).
  • V to L d are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.
  • L a to L d may be each independently a substituted or unsubstituted C1 to C10 alkylene group.
  • the cell may be represented by the following Chemical Formula 4-1 or Chemical Formula 5-1.
  • Cage Width (ca g e width) of the shell may be 6.5A to 7.5A.
  • the core may have a length of 1 nm to 3 nm.
  • the core may have a maximum absorption peak at wavelengths of 530 nm to 680 nm.
  • the core-shell dye may be represented by any one selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 19.
  • the core-shell dye may include the core and the shell in a molar ratio of 1: 1.
  • the core-shell dye may be a green dye.
  • Another embodiment provides a photosensitive resin composition comprising the compound or the core-shell dye.
  • the photosensitive resin composition may further include a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.
  • the photosensitive resin composition may further include a pigment.
  • the photosensitive resin composition may include 0.5 wt% to 10 wt% of the compound or core-shell dye, based on the total amount of the photosensitive resin composition; 0.01 wt% to 30 wt% of the binder resin; 0.01 wt% to 30 wt% of the photopolymerizable monomer; The photopolymerization initiator 0.01 to 5 weight 3 ⁇ 4>; And the balance of the solvent.
  • the photosensitive resin composition may further include a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof, including malonic acid, 3-amino ⁇ 1, 2-propanediol, a vinyl group, or a (meth) acryloxy group. It may include.
  • a color filter manufactured using the photosensitive resin composition may include.
  • FIG. 1 is a view showing the cage width (cage wi dth) of the shell represented by the formula (5-1).
  • substituted means that at least one hydrogen atom of the compound is a halogen atom (F, CI, Br, 1), hydroxy group, C1 to C20 alkoxy group, nitro group, cyano group, amine group, imino group , Azido groups, amidino groups, hydrazino groups, hydrazono groups, carbonyl groups, carbamyl groups, thiol groups, ester groups, ether groups, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C6 to C30 aryl group, C3 to C20 cycloalkyl group,.
  • F halogen atom
  • heterocycloalkyl group Unless otherwise specified in the specification, a “heterocycloalkyl group”, “heterocycloalkenyl group”, “heterocycloalkynyl group” and
  • heterocycloalkylene group is meant the presence of at least one hetero atom of N, 0, S or P in the ring compound of cycloalkyl, cycloalkenyl, cycloalkynyl and cycloalkylene, respectively.
  • R 1 is a substituted or unsubstituted C3 to C20 cycloalkyl group or represented by the following formula (2),
  • R 2 is a substituted C6 to C20 aryl group
  • R 3 and R 4 are each independently a substituted or unsubstituted C 1 to C 10 alkyl group.
  • R 1 and R 2 may be bonded to each other to form a fused ring.
  • the compound represented by Chemical Formula 1 may be used as a green dye as a compound having excellent green spectral characteristics and a high molar extinction coefficient.
  • Compound according to one embodiment is a branched alkyl functional group (different substituent represented by the formula (2)) and substituted aryl functional groups (more specifically represented by the following formula 3) is a symmetric structure with each other, thereby improving durability, As a result, a color filter having high brightness and high contrast ratio can be implemented.
  • R 2 may be a C 6 to C 20 aryl group substituted with a C 1 to C 10 alkyl group. have.
  • R 2 may be represented by the following Chemical Formula 3.
  • R 5 and R 6 are each independently a C1 to C7 alkyl group.
  • solubility in a solvent described later may be 5 or more, for example, 5 to 10.
  • the solubility can be obtained by the amount (g) of the dye (compound) dissolved in 100 g of the solvent.
  • the compound represented by Chemical Formula 1 may have excellent heat resistance. That is, the pyrolysis silver may be 20C C or more, for example, 200 ° C to 30CTC as measured by a thermogravimetric analyzer (TGA).
  • TGA thermogravimetric analyzer
  • the compound represented by Chemical Formula 1 has three resonance structures, as shown in the following scheme, but for the sake of convenience, the compound represented by Chemical Formula 1 may be represented by only one resonance structure. That is, the compound represented by Chemical Formula 1 may be represented by any one of the three resonance structures.
  • the compound represented by Chemical Formula 1 may be represented by any one selected from the group consisting of compounds represented by Chemical Formulas 1-1 to 1-7.
  • the core-shell dye may have a structure consisting of a core and a shell surrounding the core.
  • the core includes a compound represented by Chemical Formula 1.
  • the shell may be a macrocyclic compound, the shell may form a coating layer surrounding the compound represented by the formula (1).
  • the shell corresponding to the macrocyclic compound has a structure surrounding the compound represented by Chemical Formula 1, that is, having a structure in which the compound represented by Chemical Formula 1 exists inside the macrocyclic ring. It is possible to improve the durability of the core-shell dye, thereby realizing a high brightness and high contrast color filter.
  • the length of the compound represented by Formula 1 included in the core or constituting the core may be 1 nm to 3 nm, for example, 1.5 nm to 2 nm.
  • the compound represented by Formula 1 has a length within the range, it is possible to easily form a core-shell dye having a structure of a core and a shell surrounding the compound.
  • the shell which is the macrocyclic compound, may be obtained in a structure surrounding the compound represented by Chemical Formula 1.
  • the shell is difficult to form a structure surrounding the compound to be a core, it is difficult to expect the improvement of durability.
  • the compound represented by Formula 1 included in the core or constituting the core has a maximum absorption peak at a wavelength of 530 nm to 680 nm. Can be.
  • a core-shell dye using the compound represented by Formula 1 having the spectral characteristics as a core for example, as a green dye, a photosensitive resin composition for color filters having high brightness and high contrast ratio can be obtained.
  • the shell surrounding the core including the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 4 or Chemical Formula 5.
  • L a to L d are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group.
  • L a to L d may be each independently a substituted or unsubstituted C1 to C10 alkylene group.
  • the solubility is excellent, and the shell easily forms a structure surrounding the core including the compound represented by the formula (1).
  • a core-shell dye according to another embodiment may be a non-covalent bond, ie hydrogen, between an oxygen atom of a compound represented by Formula 1 and a hydrogen atom bonded to a nitrogen atom of a shell represented by Formula 4 or Formula 5 May comprise a bond.
  • the shell may be represented by, for example, the formula 4-1 or 5-1.
  • the cage width of the shell may be 6.5A to 7.5A, and the volume of the shell may be 10A to 16A.
  • the cage width means a distance inside a shell, for example, a distance between two different phenylene groups in which a methylene group is connected to both sides in a shell represented by Formula 4-1 or Formula 5-1. (See Figure 1).
  • the shell has a cage width within the above range, it is possible to obtain a core-shell dye having a structure surrounding the core comprising the compound represented by Formula 1, thereby adding the core-shell dye to the photosensitive resin composition If you do this, you will have excellent durability and high brightness
  • the branch may implement a color filter.
  • the core-shell dye may include a core including the compound represented by Chemical Formula 1 and the shell in a molar ratio of 1: 1.
  • a coating layer (shell) surrounding the core including the compound represented by Formula 1 may be well formed.
  • the core-shell dye may be represented by any one selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 19, but is not necessarily limited thereto.
  • the core-shell dye may be used alone as a green dye, or may be used in combination with a color dye.
  • the dye examples include triaryl methane dyes, anthraquinone dyes, benzylidene dyes, cyanine dyes, phthalocyanine dyes, azapopyrine dyes, indigo dyes, and xanthene dyes.
  • the core-shell dyes may also be used in combination with pigments.
  • a red pigment, a green pigment, a blue pigment, a yellow pigment, a dark pigment, or the like can be used.
  • red pigment examples include CI red pigment 254, CI red pigment 255, CI A red pigment 264, CI red pigment 270, CI red pigment 272, CI red pigment 177, CI red pigment 89, etc. are mentioned.
  • green pigment examples include CI green pigment 36, CI green pigment 7, CI green pigment 58, CI green pigment 59 and the like.
  • blue pigment examples include CI blue, pigment 15: 6, CI blue pigment 15, CI blue pigment 15: 1, CI blue pigment 15: 2, CI blue pigment 15: 3, CI blue pigment 15: 4, CI blue pigment Copper phthalocyanine pigments, such as 15: 5 and CI blue pigment 16 etc. are mentioned.
  • yellow pigment examples include isoindolin-based pigments such as CI yellow pigment 139, quinophthalone-based pigments such as CI yellow pigment 138, nickel complex pigments such as CI yellow pigment 150 and the like.
  • dark pigment examples include aniline black, perylene black, titanium black, carbon block and the like. The pigments may be used alone or in combination of two or more thereof, but is not limited to these examples.
  • the pigment may be included in the photosensitive resin composition for color filters in the form of a dispersion.
  • a dispersion may be composed of the pigment and a solvent, a dispersant, a dispersion resin and the like.
  • Ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclonucleanone, propylene glycol methyl ether, etc. may be used as the solvent, and among these, propylene glycol methyl ether acetate may be used.
  • the dispersant helps to uniformly disperse the pigment in the dispersion, and can be used for both nonionic, anionic or cationic dispersants.
  • polyalkylene glycol or esters thereof polyoxy alkylene, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkyl amide alkylene oxide additions
  • Water, alkyl amine, etc. can be used, These can be used individually or in mixture of 2 or more types.
  • the dispersion resin may use an acrylic resin including a carboxyl group, which may not only improve the stability of the pigment dispersion but also improve the pattern of the pixel.
  • the core-shell dye and the pigment When used in combination, they may be used in a weight ratio of 1: 9 to 9: 1, specifically, in a weight ratio of 3: 7 to 7: 3. When mixed in the weight ratio range, it may have a high brightness and contrast ratio while maintaining color characteristics.
  • a photosensitive resin composition including the compound represented by Formula 1 or the core-shell dye is provided.
  • the photosensitive resin composition includes (A) a colorant (compound represented by Formula 1 or the core-shell dye), (B) binder resin, (C) photopolymerizable monomer, (D) photopolymerization initiator, and (E) solvent. can do.
  • the colorant may include the compound represented by Chemical Formula 1 and / or the core-shell dye, and the compound represented by Chemical Formula 1 and / or the core-shell dye has been described above.
  • the colorant may further include a pigment in addition to the compound represented by Chemical Formula 1 and / or the core-shell dye, which has been described above.
  • the compound represented by Chemical Formula 1 and / or the core-shell dye may be included in an amount of 0.5 wt% to 10 wt%, such as 0.5 wt% to 5 wt%, based on the total amount of the photosensitive resin composition for color filters.
  • the core-shell dye is used within the above range, it is possible to express high brightness and contrast ratio in a desired color coordinate.
  • the binder resin is a copolymer of the first ethylenically unsaturated monomer and the second ethylenically unsaturated monomer copolymerizable therewith, and may be a resin including one or more acrylic repeating units.
  • the first ethylenically unsaturated monomer contains one or more carboxyl groups Ethylenic unsaturated monomer, specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.
  • the first ethylenically unsaturated monomer may be included in an amount of 5 wt% to 50 wt%, such as 10 wt% to 40 wt%, based on the total amount of the alkali-soluble resin.
  • the C2-ethylenically unsaturated monomers include aromatic vinyl compounds such as styrene, d-methylstyrene, vinylluene, and vinylbenzylmethyl ether; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate,
  • Unsaturated carboxylic ester compounds such as 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate, cyclonuclear (meth) acrylate, and phenyl (meth) acrylate; Unsaturated carboxylic acid amino alkyl ester compounds, such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds, such as vinyl acetate and a vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; Vinyl cyanide compounds such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These etc. can be mentioned, These can be used individually or in mixture of 2 or more.
  • binder resin examples include methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer And methacrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, etc. are mentioned, It is not limited to these, These can also be used individually or in combination of 2 or more types.
  • the weight average molecular weight of the binder resin is from 3, 000 g / mol to 150, 000 g / mol, such as 5, 000 g / mol to 50, 000 g / mol, such as 20, 000 g / mol to 30, 000 g / can be nl.
  • the acid value of the binder resin may be 15 mgKOH / g to 60 mgKOH / g, such as 20 mgKOH / g to 50 mgKOH / g. When the acid value of the binder resin is within the above range, an excellent pixel resolution can be obtained.
  • the binder resin may be included in an amount of 0.01 wt% to 30 wt%, such as 5 wt% to 20 wt%, based on the total amount of the photosensitive resin composition. In the case where the binder resin is included in the above range, the developability and the crosslinkability of the color filter may be improved to obtain excellent surface smoothness.
  • a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond may be used. Since the photopolymerizable monomer has the ethylenically unsaturated double bond, the polymerizable monomer is formed during exposure in the pattern forming process, thereby forming a pattern having excellent heat resistance, light resistance, and chemical resistance.
  • photopolymerizable monomer examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate and neopentyl glycol Di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-nucleic acid diol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylic Laterate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol nucleated (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaery Tree to tri (meth) acrylate, dipentaerythritol penta
  • Examples of commercially available products of the photopolymerizable monomer are as follows. remind Examples of the monofunctional ester of (meth) acrylic acid include Aronix M-101®, M-111®, M-114®, and the like manufactured by Toagosei Kagaku Kogyo Co., Ltd .; KAYARAD TC-110S®, TC-120S®, etc. of Nihon Kayak Co., Ltd .; And V-158® and V-2311® by Osaka Yuki Kagaku Kogyo Co., Ltd.
  • Examples of the difunctional ester of (meth) acrylic acid include, but are not limited to, Aronix M-210®, M-240®, M-6200®, manufactured by Toagosei Chemical Industries, Ltd .; Nihon Kayak Co., Ltd. KAYARAD HDDA®, HX-220®, R-604®, etc .; The V-260®, V-312®, and V-335 HP® by Osaka Yuki Chemical Co., Ltd. are mentioned.
  • Examples of the trifunctional ester of (meth) acrylic acid include Aronix M-309®, Copper M-400®, Copper M-405®, Copper M-450®, and Copper M, manufactured by Toagosei Chemical Industries, Ltd.
  • the photopolymerizable monomer may be used by treating with an acid anhydride in order to impart better developability.
  • the photopolymerizable monomer may be included in an amount of 0.1 wt% to 30 wt%, such as 5 wt%> to 20 wt%, based on the total amount of the photosensitive resin composition.
  • the photopolymerizable monomer is included in the above range, it is excellent in pattern characteristics and developability when manufacturing a color filter.
  • an acetophenone compound As the photopolymerization initiator, an acetophenone compound, a benzophenone compound, a thioxanthone S compound, a benzoin compound, a triazine compound, an oxime compound or the like can be used.
  • acetophenone-based compound examples include 2,2 diethoxy acetophenone, 2,2 dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone and pt-butyldichloro Acetophenone 4-chloro acetophenone , 2 , 2′-dichloro-4-phenoxy acetophenone , 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1-one,
  • 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one etc. are mentioned.
  • benzophenone compounds include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4 '-Bis (diethylamino) benzophenone, 4'4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone,
  • thioxanthone compound examples include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone etc. are mentioned.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethyl ketal and the like.
  • triazine-based compound examples include 2,4,6-trichloro ⁇ s-triazine, 2-phenyl 4, 6-bis (trichloromethyl) -S-triazine,
  • the photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, a fluorene compound, or the like.
  • the photopolymerization initiator may be included in an amount of 0.1 wt% to 5 wt%, such as 1 wt% to 3 wt%, based on the total amount of the photosensitive resin composition.
  • the photopolymerization initiator is included in the above range, the photopolymerization occurs during exposure in the pattern forming process for manufacturing the color filter, thereby providing excellent sensitivity and improving transmittance.
  • the solvent is not particularly limited, and specific examples thereof include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether, and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Methyl ethyl carbye, diethyl carbyl, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether H, and the like.
  • alcohols such as methanol and ethanol
  • Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate
  • Aromatic hydrocarbons such as toluene and xylene
  • Methyl ethyl ketone , cyclonucleanone
  • 4-hydroxy ketones such as 4-methyl-2-pentanone, methyl -n-propyl ketone, methyl -n-butylkenone, methyl _ n _ amyl ketone and 2-heptanone; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, -n-butyl acetate and isobutyl acetate; Lactic acid alkyl esters such as methyl lactate ethyl lactate; Hydroxyacetic acid alkyl esters such as methyl hydroxyacetate, ethyl hydroxyacetate and butyl hydroxyacetate; Meoxymethyl Acetate, Mesoxyethyl Acetate, Meoxybutyl Acetate, Elooxymethyl Acetate, Eryoxyethyl Acetate Acetic alkoxy alkyl esters, such as these; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate
  • ⁇ -methylacetamide, ⁇ , ⁇ -dimethylacetamide, ⁇ -methylpyridone dimethyl sulfoxide, benzyl ethyl ether, dinuclear silether, acetylacetone, isophorone, capronic acid, caprylic acid, 1-octanol , 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc., used alone or in combination of two or more Can be used in combination.
  • ketones such as cyclonucleone
  • Glycol ethers such as ethylene glycol monoethyl ether
  • Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate
  • Esters such as 2-hydroxyethyl propionate
  • Diethylene glycols such as diethylene glycol monomethyl ether
  • Propylene glycol alkylether acetates can be used.
  • the solvent may be included in the remainder with respect to the total amount of the photosensitive resin composition, and specifically, may be included in the 20 to 3 ⁇ 4 to 90% by weight.
  • the coating property of the photosensitive resin composition is excellent, Excellent flatness can be maintained in a film having a thickness of 3im or more.
  • the photosensitive resin composition may be used to prevent stains or spots upon application, to improve leveling performance, and to prevent generation of residues by undeveloped malonic acid; 3-amino-1, 2-propanediol; Silane coupling agent containing a vinyl group or a (meth) acryloxy group; Leveling agents; Fluorine-based surfactants; Additives, such as a radical polymerization initiator, may be further included.
  • the photosensitive resin composition may further include an additive such as an epoxy compound in order to improve adhesiveness with a substrate.
  • a phenol novolak epoxy compound a tetramethyl biphenyl epoxy compound, a bisphenol-A epoxy compound, an alicyclic epoxy compound, or a combination thereof is mentioned.
  • Another embodiment provides a color filter manufactured using the photosensitive resin composition described above.
  • the manufacturing method of the color filter is as follows.
  • suitable methods such as spin coating and slit coating of the photosensitive resin composition for color filters described above are performed. Each using a thickness of 3.1 zm to 3.4.
  • light is irradiated to form a pattern required for the color filter.
  • the coating layer is treated with an alkali developer, so that the unilluminated portion of the coating layer is dissolved to form a pattern necessary for the color filter.
  • crack resistance, solvent resistance, and the like can be further improved by heating the image pattern obtained by development again or curing by active ray irradiation or the like.
  • 2,4-dimethyldiphenylamine (10 mol), 2-iodine propane (10 mol) and sodium hydride (10 mol) were added to ⁇ , ⁇ -dimethylformamide and heated to 80 ° C. and stirred for 24 hours.
  • Ethyl acetate was added to the solution, washed twice with water, and the organic layer was extracted. The extracted organic layer was distilled under reduced pressure and separated by column chromatography.
  • the compound represented by the formula (1-2) was dissolved in 600 mL chloroform solvent, and triethylamine (50 mmol) was added thereto.
  • 2,6-pyr idinedicarbonyl dichloride (20 ⁇ ol) and p-xylylenedi amine (20 mmol) are dissolved in 60 mL chloroform and added dropwise at room temperature for 5 hours. After 12 hours, the product was distilled under reduced pressure, separated by column chromatography, and the core-shell dye represented by the following Chemical Formula 9 was combined.
  • Compound (5 ′ ol) represented by Formula 1-3 was dissolved in 600 mL chloroform solvent. Fu, Isophthaloyl chloride (20 ⁇ ol) and p-xylylenediamine (20 ⁇ ol) are dissolved in 60 mL chloroform and simultaneously added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to synthesize a core-shell dye represented by the following Chemical Formula 10.
  • Synthesis Example 19 Synthesis of Core-Shell Dye represented by Chemical Formula 17
  • Compound (5 mmol) represented by Chemical Formula 1-6 was dissolved in 600 mL chloroform solvent, and triethylamine (50 ⁇ l) was added thereto.
  • 2,6-pyridinedicarbonyl dichloride (20 ⁇ l) and p-xylylenediamine (20 ⁇ l) were dissolved in 60 mL chloroform and added dropwise for 5 hours in phase silver. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to synthesize a core-shell dye represented by Chemical Formula 17.
  • the compound represented by the formula (1-7) (5 'ol) is dissolved in 600 mL chloroform solvent, and then triethylamine (50' ol) is added thereto.
  • 2,6-pyr idinedi carbonyl dichloride (20 ⁇ ol) and p_xylylenediamine (20 ⁇ ol) are dissolved in 60 mL chloroform and added dropwise at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to synthesize a core-shell dye represented by the following Chemical Formula 19.
  • the core-shell dye was obtained in a structure in which the compound represented by the formula (X) surrounds the compound represented by the formula (Y).
  • Methacrylic acid / benzyl methacrylate copolymer having a weight average molecular weight of 22, 000 g / m (combined weight ratio 15wt% / 85wt%)
  • each component was mixed with the composition of following Tables 1-4, and the photosensitive resin composition was produced. Specifically, after dissolving the photopolymerization initiator in a solvent, the mixture is stirred at room temperature for 2 hours, added with a dye (or pigment dispersion), stirred for 30 minutes, and then the binder resin and the photopolymerizable monomer are added thereto at room temperature for 2 hours. Stirred. The solution was filtered three times to remove impurities to prepare a photosensitive resin composition.
  • the photosensitive resin composition prepared in Examples 1 to 21 and Comparative Examples 1 to 8 was applied at a thickness of 1 to a glass substrate having a thickness of 1 ⁇ by degreasing, and 2 minutes on a hot plate at 90 ° C. Drying to give a coating. Subsequently, the coating film was exposed to light using a high pressure mercury lamp having a dominant wavelength of 365 nm, and then dried in a hot air circulation drying furnace at 20C C for 5 minutes.
  • the pixel layer is a spectrophotometer (MCPD3000, Otsuka electronic) The brightness and contrast ratio were measured using the results, and the results are shown in Table 5 below.
  • the photosensitive resin composition prepared in Examples 8 to 21 and Comparative Examples 1 to 8 was applied on a glass substrate having a thickness of 1 ⁇ by degreasing washing, and then on a hot plate at 90 ° C. Drying for 2 minutes gave a coating. Subsequently, the coating film was exposed to light using a high pressure mercury lamp having a dominant wavelength of 365 nm, dried for 20 minutes at 200 ° C. in Aubon, and the change of color coordinates was measured using a spectrophotometer (MCPD3000, Otsuka electronic). The durability was confirmed, and the results are shown in Table 6 below. Durability Evaluation Criteria
  • ⁇ color coordinate change value is 0.003 or more and 0.005 or less
  • Comparative Example 8 X From Table 6, Examples 8 to 21 including the core-shell dye according to the embodiment, and Comparative Examples 1 to 8 and do not include the core-shell dye In comparison, it can be seen that the durability is increased.
  • the present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person of ordinary skill in the art to which the present invention pertains does not change the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

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KR102575019B1 (ko) * 2020-02-24 2023-09-04 삼성에스디아이 주식회사 코어-쉘 화합물, 이를 포함하는 감광성 수지 조성물, 감광성 수지막, 컬러필터 및 cmos 이미지 센서
TWI802026B (zh) * 2020-09-29 2023-05-11 南韓商三星Ｓｄｉ股份有限公司 核-殼化合物、包括其的感光性樹脂組成物、感光性樹脂層、彩色濾光片及cmos影像感測器
CN116472315A (zh) * 2020-12-22 2023-07-21 三星Sdi株式会社 核壳染料、包含其的感光性树脂组合物、感光性树脂膜、滤色器、以及cmos图像传感器
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KR20220169896A (ko) * 2021-06-21 2022-12-28 삼성에스디아이 주식회사 코어-쉘 화합물, 이를 포함하는 감광성 수지 조성물, 감광성 수지막, 컬러필터 및 cmos 이미지 센서
KR20230013508A (ko) * 2021-07-19 2023-01-26 삼성에스디아이 주식회사 코어-쉘 화합물, 이를 포함하는 감광성 수지 조성물, 감광성 수지막, 컬러필터 및 디스플레이 장치
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